Create A Personalized Family Fun Day In May!

As we wrap up the month of May, I started thinking about how special this month is and how it doesn’t really get the fanfare it deserves! Not only does May host Mother’s Day and Memorial Day, it’s also when schools let out for summer break and when college students graduate. May also boasts long days and late sunsets (love!). It’s a time when businesses stay open longer (thank you froyo shop for letting me indulge my cravings until 10pm!). And, it’s the one month out of the whole year where the weather is perfectly warm without crossing over into the sweltering summer heat that’ll be upon us in just a few short weeks. Add that up and what does it all mean? It means that May is the perfect month to gather your relatives for Family Fun Day (a.k.a. Family Reunion)!

Show Gratitude For Those You Love

Create A Personalized Family Fun Day In May! - the letters L O V E in red and purple

We give thanks to military heroes this time of year but there is more than one way to fight for those you love, right? (Yes, my darling daughter, that would be staying up all night to help you with your school project!) We give thanks to moms this month, but then wait another four weeks to give a shout out to the dads. I say we start rolling a bunch of different occasions into one big fat fabulous celebration and make an annual tradition out of family fun day every May to recognize the love and support of family year round! Sound too complicated? Doesn’t have to be!

The Logistics Of Family Fun Day

Create A Personalized Family Fun Day In May! - Coco and grandpa

I know, modern families are spread out all over the globe and not everyone will be able to attend. If you make it known that your goal going forward is to have an event every year in May, it takes the pressure off people because even if they can’t make the first family fun day, they can plan for one down the road.

Create A Personalized Family Fun Day In May! - Marley sitting at her desk at the office

If you’re the brains behind the operation and this is your first rodeo so to speak, a lot will rest on your shoulders. But that’s okay! Since you’re in charge, you can make it as simple or complicated as you like! Here are some things to consider:

Number Of People

This plays a big role in how simple or complicated things are going to get! It’s fairly easy to wrangle 10 people together. More than that and things can get difficult. If you have a very large family or want distant relatives to join in the festivities, the event you plan should accommodate the size of the group. That leads us to…

Destination & Accommodations

If people are visiting from out of town, you’re better off trying to make family fun “day” into family fun “weekend.” That means you’ll have to think about lodging for travelers. Most people’s homes can’t sleep 20, and boy will you have a line of people waiting to shower! This means 1 of 3 things: you’re either going to need rooms at a nearby hotel (if your home is going to be the meeting hub); or, you’ll need to rent a large home (Airbnb is perfect for this!) that can accommodate your entire party “staycation” style; or, your group will have to agree upon a destination event where everyone will be staying at the same location be that a hotel, ranch, lodge or campsite.


How much do you want to spend? If everyone lives locally, there won’t be the expense of airfare to fly somewhere. For others, travel costs will be a factor. Be considerate of people’s budget. You, as the world-renowned plastic surgeon, may easily be able to afford to fly to New York for the weekend, but that’s a costly endeavor for students and those living on a teacher’s salary! Try to find something everyone in the group can afford to do. (Unless, of course, your last name is Rockefeller, in which case, call me (!) and I’m going to have so much fun planning your family day!)

Decide how you want to handle the expense. Every family has cheapskates (why, yes… yes, they do!), freeloaders, and spendthrifts – you know your family best, figure accordingly! Divide the cost evenly among attendees, or simply host something with the idea that each year someone else will host and pick up the tab. Again, if you do something annually, people will feel much less pressure in the finance department.

Create A Tradition With Trees, Raffles & Custom Swag

Create A Personalized Family Fun Day In May! - leaves placed on a geometric shape

Create a family tree on paper or fabric with each person’s name written on a re-usable “leaf” made from colored paper or felt or fabric of your choosing that you include in the invitation itself. Those who RSVP to attend simply send the leaf back to let you know they’re coming! Otherwise they can hold on to it until the next annual family fun day.

Increase the excitement of coming by letting everyone know their leaf will be put in a jar for a prize raffle and one name will be drawn at the end of the day for a gift giveaway! The gift can be as big or little as you like. From a “movie prize package” that includes a theater gift card and box of milk duds to a bottle of wine or kitchen gadget, the raffle is part of the fun.

Okay, I’ll be honest, I think matchy-matchy t-shirts with family names on them are pretty lame! But there’s nothing wrong with custom apparel that’s super cool! If you have any artists in the family (really, there has to be at least one!) have them create a “family crest” that features whimsical elements that reflect your family’s interests or heritage – Irish? Have one of the icons be a pint of beer! Italian? Put a plate of spaghetti in your crest! Are there six nurses among you? Stethoscopes work for that. Get creative and then design a crest you can use as a logo on a tote bag, t-shirt or water bottle. There are hundreds of online shops that customize that kind of thing. After a few reunions, you’ll have a whole cool collection of family-centric mementoes!

Activities For Family Fun Day!

Okay, you’ve planned and prepped and now you actually have to do something together! Here are some suggestions for family fun day, starting with the least complicated, least expensive first. We’ll work our way up from there!

Beach Blanket Bash

Create A Personalized Family Fun Day In May! - beach

If you live along the coast, have everyone in your party meet at the beach. Set up tables and a canopy or tent strung with twinkle lights to make it official! Barbecue, make s’mores and bring blow up rafts and toys for people to play games, splash in the water, and soak up some sun. Have the musicians in the group bring guitars for a little nighttime music under the stars for later.

Rent A Pizza Oven

Create A Personalized Family Fun Day In May! - pizza

Yes, you can actually rent these and set them up in your yard! Set up a pizza making station for toppings and reunite with family over a slice of pie that you make yourself! Then, after the sun sets, do an old fashioned slide show on a bedsheet or wall (have people send you picture files in advance so you can put it together) that shows what everyone’s been up to in their neck of the woods while you enjoy self-serve ice cream sundaes! (Want more suggestions like this? Check out our 65 Super Secret Party Tips Guide!)  A lot of time people live long distances apart and cousins on opposite sides of the country may not really even know one another. The slide show is a nice way for family members to get acquainted, see where they work and live, what they do for a living, learn their hobbies, their pets, their car (even if it’s the subway!). Make it fun and silly and a focal point of the day.

Limousine & Karaoke

Create A Personalized Family Fun Day In May! - Marley singing at her birthday party

Taking a limo ride is fun and special (especially for the kids!) and it lets everyone start imbibing on the drive to your destination! Frankly, if you hate your singing voice (like me!) and are embarrassed to stand up in front of a group, drinking on the drive over is, like, REALLY important! And, super fun! If you live in a big city it should be easy to find karaoke bars that have private booths and food service designed specifically for large parties. If those aren’t available, check your local bar listings. You’re bound to find any number of venues that host karaoke.

Hot Air Balloon Ride

Create A Personalized Family Fun Day In May! - hot air balloons

Where I live in California, there are hot air balloon rides in a number of places from San Diego and Los Angeles to Napa Valley. But many other states offer them as well. Nevada and Arizona, for one. You can fly over the Vegas strip or the Grand Canyon. In Utah you can soar over the national parks. There are also some in Colorado, New Mexico, Vermont, New York, Wisconsin, Florida, and Chicago, Illinois. Balloon rides usually include a glass of Champagne and/or lunch included in the price, which will run you anywhere from $150 – $300 a person.

Party Mansion

Create A Personalized Family Fun Day In May! - entrance to a beautiful home

If you have a large family and there isn’t any way to comfortably cram everybody in to your home, Airbnb comes in handy! There you can rent large homes that can sleep dozens of people. Plus, you get to pretend you’re rockstar rich! Rent a large home with gourmet kitchen and swimming pool and just indulge in how the other half lives. You can have your weekend catered, or cook yourself. You might also think about hiring a local band so that you have live music for a few hours.

Horse Ranch Weekend

Create A Personalized Family Fun Day In May! - girl riding a horse

As mentioned before, if people are traveling long distances or from many different locations it’s usually better to meet up someplace for the weekend. Ranches are great options because the lodging and activities are in the same place. Ride horses, cook by campfire, hike nearby trails and just unwind in nature.

Glamping = Glamorous Camping

Create A Personalized Family Fun Day In May! - glamping tents

Now you don’t have to sleep on the dirt or in sleeping bags on jagged rocks that hurt your back! Get all the fun of the outdoors in a fancy schmancy tent or yurt that has beds and toilets (!) #ThankYouBabyJesus. Some services even provide a chef who will come and prepare meals by campfire. Even though you’re technically ‘roughing it’ glamping sites are priced on par with four star hotels. Check out these four options in Hawaii, Ireland, Australia and New Zealand featured on AllTheRooms blog! (I’m DYING to try the one down under! It includes hot tubs and spa treatments!) You’ll definitely want to follow their Instagram page for the most inspiring, swoon-worthy travel pics you’ll ever lay eyes on!

Private Rail Car Train Adventure

Create A Personalized Family Fun Day In May! - private rail car

Okay, this is going to set you back some serious cash, but oh-my-gawd-how-fun would it be to ride in a refurbished train car! Privately owned rail cars are attached to passenger trains so you’re traveling the regular line but in a posh setting with your own private attendants to mix you drinks, serve food, and see to your needs. Curious? Luxury Train Club is a company that has rail cars in North America, Europe and Asia.

We’ve got lots of other ideas that can help you with your next family fun day. Download our FREE Party Tips Guide for the most comprehensive list of entertainment tips you’ll ever find! (Or need!)

Pink clickable rectangle with text overlay - "Click here for party tips!"

P.S. If you liked these Family Fun Day suggestions, you’ll love these other tips!

Drink Trends For Coffee, Beer & Spirits

20 Ways To Host A Wine Tasting Party!

Plated Desserts You’ll Want To Save Room For!

What’s your funniest family moment? Really, I want to know! Tell us in the comments below!

Create A Personalized Family Fun Day In May! - Pinterest title image
Love this? Pin it to your Events Board.

One response to “Create A Personalized Family Fun Day In May!”

  1. Maharajas’ Express – an initiative of Indian Railways Catering and Tourism Corporation (IRCTC) – is the latest luxury train to be introduced in India. Dubbed India’s equivalent to the Orient Express of Europe, this Maharaja train is rated by prestigious travel magazines and luxury guides as one of the greatest rail journeys in the world.

Leave a Reply

Your email address will not be published. Required fields are marked *

Welcome to my sparkly world as a celebrity event planner, TV contributor & author obsessed with Louboutins, glitter + travel. Forever in search of the perfect donut. If you like something pin it!